


Butch

by Vexed_Wench



Category: Supernatural
Genre: Community: fanbingo, Community: hentai_contest, Crossdressing Dean, Crossdressing Kink, Fluff and Smut, M/M
Language: English
Status: Completed
Published: 2015-05-31
Updated: 2015-05-31
Packaged: 2018-04-02 03:09:20
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,583
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4043548
Author URL: https://archiveofourown.org/users/Vexed_Wench/pseuds/Vexed_Wench
Summary: <blockquote class="userstuff">
              <p>Sam Tries to make Dean's secret fantasy come true. </p>
<p>Written for the prompts: Genderplay at  the hentai_contest.<br/>The Same Only Different Canon A/U Square on my fanbingo Bingo Card.</p>
            </blockquote>





	Butch

**Author's Note:**

  * For [spiralicious](https://archiveofourown.org/users/spiralicious/gifts).



Sam wiped his sweaty palms down the sides of his jeans. He couldn't remember the last time he felt this nervous in a mall with cash in his pocket. He was calmer than this the Christmas he decided he wanted to get Dean something special and stole him a new outfit. This time he bought everything in the many bags he was now carrying.

Funny that it was his love of Dean that had brought him back to leaving the mall on the verge of a panic attack. He wanted to do something special for his brother. He knew things had been strained between them for a while. He knew in his head that it wasn't the first time they had a fight that was bad enough that they had trouble navigating their way back to each other. They loved too fiercely to not be able to push each other’s buttons that badly. Their love was twisted and complicated and the fact that they were brothers was the least of the reason.

Dean would joke that their issues had issues, and Sam never could argue with that.

He doubted anyone could've lived through what they had and remained sane. Mortals should never have laid eyes on Heaven, Hell, Purgatory, or Lucifer's Cage. Not to mention the possessions, being soulless, being turned by a vamp, or finding out they were the true vessels to a couple of the most powerful angels in any fucking garrison.

Sam thought the fact that they were not a drooling mess in a corner of some dusty mental hospital was a win on both of their parts.

He quickly walked to the car and stashed the bags in the back seat. He tried to tell himself that Dean couldn't see him. Even if he could, he knew that his brother would be pissed off at first, but eventually, he would see Sam was right.

The clues were there, if Sam had only bothered to open his eyes. The first sign was the time Dean came to bed and his lips were a little shimmery and red. Sam had been with enough women to know lip gloss when he saw it. He was dumb enough to comment on it after exchanging a few kisses with him. Dean froze up and mumbled something about grabbing the wrong Chap Stick, and slunk off to the other bed.

Sam slept horribly that night. He promised himself that he wouldn't do anything that stupid again.

The next time, Dean had slipped under the blankets and was wearing an honest to goodness Spedo. Sam wasn't awake and made a joke about not needing a vacation, if he was willing to be the cabana boy.

The thing that clenched it in his mind was when Sam had returned to the room early and found Dean trying on the wig he used when they cosplayed and helped Charlie win her epic battle.

He had no clue how long Dean had wanted something like this. He was sorry he hadn't made Dean feel comfortable enough to talk about it. He did remind himself that talking was never Dean's strong suit. His brother was a man of action, not a man of words.

Sam pulled into the parking lot of the crappy motel they were staying in. He made Dean take him out for the weekend, claiming he was going stir crazy in the bunker. The truth was he wanted to be in a new place so Dean wouldn't be worried about people knowing what they had been up to. He knew how sensitive Dean could be when it came to his macho side. His brother was like a burnt marshmallow, crunchy on the outside and soft and gooey in the middle.

 

"Where's the food?" Dean asked him when he saw Sam was loaded down with shopping bags, but not one take out bag with a restaurant’s logo on it.

"I thought we could fool around a little first."

"Okay, what brought that on? Not that I am complaining mind you, but something at the local outlet mall got you hot and bothered? Do I need to go to the local geek shop and tell them all you are very _taken_?"

"What? No, it's not like that," Sam told him and made his way over to the side of the bed.

Sam straddled Dean on the bed and scattered the shopping bags just out of reach.

"Sam?"

"Hush, just lay back and listen."

"Oh, a bedtime story. I think you have it backwards. It was always my job to tell you a story and tuck you in at night."

"Are you going to listen, or do you want to just forget it?"

"Go ahead, amaze me."

"Once upon a time there was a man named _Butch_. Butch was the biggest badass anyone had ever seen. He saved the world from more big bad things than most people could even dream up in their most horrific nightmares. He knew how to kill every evil son of a bitch that ever dared to cross his path. He was the most loyal and brave man to ever walk on any of the realms.

What makes him even more special was the part of Butch that he kept hidden from most of the world. The part that he buried so deep not many people would ever be able to find it.

The few people that knew the real Butch knew why he did it. They all knew that his dad had expectations of him that no little kid could ever meet.

Poor Butch, he was cursed with a pain in the ass little brother.

So while someone should've been taking care of him, and making him the center of their world, he was raising the pain in the ass. Now P.I.A. loves his butch beyond all reason and he knows Butch loves him back. P.I.A realized that it wasn't too late to cherish Butch." Sam stopped there and leaned down to kiss Dean while he also rummaged around in one of the bags for the red lip stain with glitter.

He slowly dragged the tube across Dean's bottom lip, and then traced the top.

Sam grinned at his own handy work.

"Make up? Glittery make up? What the fuck are you playing at?"

"I was thinking I could show you the helpful hints the nice sales guy at the cosmetic counter gave me. He taught me how to make sure you looked glamorous and sexy and not like a reject from the _RuPual’s Drag Race_."

"You went to the mall to buy things for me? Why do you want me to be girly?" Sam wasn't dumb. He knew Dean wanted to pick a fight so one of them would storm off and the matter would then be dropped, never to be brought up again.

"I was just thinking we could try something new. I don't want you to be all _girly_. I like that you're a guy. I really like your dick. I was thinking it would be fun to play with your dick while it was trapped in a pair of silk panties. I found these, do they scream girly? They are black satin and they do have a matching bra." Sam laid both items on Dean's chest.

"You don't have to do anything you don't want to do. I thought you might get a kick out of it. We are far enough from home that no one will recognize us. If you want to go out and get a drink, we could. You could be the bad ass bitch with the muscle car and the awesome pool skills. If you’d rather role-play a sensitive girl, I am sure I can be butch for the night. I can work on picking up a nice, sweet girl like you. Bring you back here and have fun making a mess of you. No matter what, you will always be my kick ass and take names big brother. The same one that I will always want to pin me down and fuck me 'till I come so hard I forget my own goddamn name."

"Damn right you will. I am the best you've ever had."

"Yes, you are. I know it's corny, but you are my walking talking fantasy. I thought we could try this. Let me pamper you for a bit. No one ever has to know."

"You did bother to learn how to do this the right way. I guess we shouldn't let all that new found knowledge go to waste. You promise I will not look like the rejected drag queens? You know, some of them ain't bad."

"Dean, you just want to get drunk with Bianca Del Rio."

"She is awesome! If she promised to keep the _clown realness_ to a minimum, I guess you could tag along."

"Do you want to go get a drink or just order pizza?"

"Fuck that, I am an expensive girl. You will be forking out plenty of cash for my happiness, Bitch. Show me what else you bought me. We have a bar to get to, followed by a _really_ expensive dinner. If you are a very good boy, I might put out. Maybe."

Sam wondered why he thought he would actually be in charge of their night. History should've taught him better.

No matter what, he had a feeling they would be having more out of town date nights.


End file.
